14 Chicago Songs, Ranked as a Band Career Guide

Inside this ranking: 15 headline-making yachts, following the source's published order and reported estimates. Prices can change and should be read as editorial estimates rather than live appraisals.

• Two Major Chicago Eras, One Band — Two Major Chicago Eras, One Band. Early Chicago stretched rock songs with horns, jazz harmony, political observation, and suites; later Chicago became a precision ballad and pop institution.
• 14. Stay the Night — 14. Stay the Night. A muscular rhythm track and bright eighties production show Chicago adapting to the video-driven rock-pop moment.
• 13. Look Away — 13. Look Away. A strong outside-written power ballad and Bill Champlin's lead vocal carried Chicago into another late-eighties chapter.
• 12. You're the Inspiration — 12. You're the Inspiration. Warm keyboard production and carefully blended vocals make this one of Chicago's clearest adult-contemporary ballads.

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